


it can happen so fast, or a little bit late (timing is everything)

by sarcastic_fina



Category: Arrow (TV 2012)
Genre: AU, babysitter trope, does the 'underage' tag apply there? archive warnings are complicated, lovesick puppy with a crush oliver, teenage fic
Language: English
Status: Completed
Published: 2014-03-17
Updated: 2014-03-17
Packaged: 2018-01-16 00:55:28
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply, Underage
Chapters: 1
Words: 8,476
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1325701
Author URL: https://archiveofourown.org/users/sarcastic_fina/pseuds/sarcastic_fina
Summary: <blockquote class="userstuff">
              <p>(au) It's clichéd, of course, but Oliver starts crushing on his little sister's babysitter the exact same moment he meets her. He thought falling in love was supposed to be easy; it's not.</p>
            </blockquote>





	it can happen so fast, or a little bit late (timing is everything)

**Author's Note:**

> (1) [gif prompt](http://oi62.tinypic.com/2zz57pu.jpg) \+ olicity + au + felicity is oliver's first kiss - **jodi** (submission)  
>  (2) babysitter trope: felicity babysits thea, oliver ditches partying to hang out with the pretty babysitter! ;) – **anonymous** (ask)
> 
>  **polyvore** : [outfit one](http://www.polyvore.com/felicity_oneshot_7a/set?id=116428464), [outfit two](http://www.polyvore.com/felicity_oneshot_7b/set?id=116433357)

When Oliver met Felicity, he was fifteen.

She was two years older and greeted him with a bright grin and a, "Hey, I'm here to babysit Thea...?"

He was pretty sure he fell in love on sight.

She was cute. In that bubbly, sweet, girl-next-door kind of way that exactly  _zero_ of the girls he had plastered on his walls were. He considered his preference to be more of the overtly sexy variety. Hot chicks in leather straddling motorcycles or in bikinis on the sand, tugging their tops down just enough to tease.

Felicity ranged between comfortable jeans that hugged an ass that would make the most unreligious man pray and skirts that had him cornering the market in Lubriderm.

From the moment she walked in, her pale blue skirt bouncing against her thighs, he was hooked. At first it was just the surface stuff. The babysitter fantasy wasn't new by any means and Oliver was starting to see the appeal. But then there were other things, like how her laugh sounded and how cute she was when she rambled and it definitely didn't help that she was actually a great babysitter who considered taking care of Thea a gift.

All bright smiles and rosy cheeks, Felicity was quick to offer up ideas for crafts and baking and fun games they could play. Oliver was always just a tiny bit surprised when the blonde beauty traded any type of conversation with him in for entertaining a bubbly five year old. But there she was, multiple times a week, greeting him brightly, because he always beat the staff to the door when he knew she was coming over, letting him help her with her jacket and trading small talk until Thea appeared, hot on his heels and eager to drag Felicity away for a tea party or to tell her all about her day. And Felicity never complained, she just waved a hand back at Oliver and skipped off with Thea. Oliver wasn't quite used to that. He couldn't think of a time in his life when anybody overlooked for him anyone, let alone his five year old sister.

Thea fell in love with her almost as quickly as Oliver did, only a different level entirely. She considered Felicity a princess and told him all the time about how pretty and smart and funny she was. As soon a she left, Thea was beside him, telling him every single detail of what they'd done that day. He shamelessly asked his sister for details about her – did she have a boyfriend, did she ever ask about him – not that it ever really got him anywhere. It wasn't like Felicity was going to confide anything to a five-year-old, but she didn't go to his school and the brief few minutes he got with her when she first arrived only felt like a small taste of something so much bigger.

That was probably the first sign that this was going to be different.

* * *

He'd be lying if he said he didn't start spending a lot of time at home on nights he knew Felicity would be over to watch Thea.

"Not that I'm trying to talk myself out of a job, but, if you're going to be here, why exactly do your parents need me around?" she wondered, smiling up at him from her seat on the couch. She'd put a cranky Thea to bed a half hour earlier and was now trying to get some homework done before his parents came home.

Oliver liked to think he was smart. He also liked to think he was a good liar. But when Felicity was asking him a question he had no convincing answer for, he froze. His tongue seemed to balloon in his mouth, thick with everything he wanted to say but knew he shouldn't. Like ' _they don't know I'm here. I'm supposed to be out with Tommy but you look so pretty in your pink sweater and I forgot to actually leave_ ' and ' _I listened to you read Thea a bedtime story because I like the voices you make for the characters and I'm possibly a ten on the pathetic scale'_ and ' _I've never liked anybody this much and now I don't know what to do or how to tell you because usually girls let me know when they want me and I just go with it and oh my god, is your rambling actually contagious?_ '

Brows furrowed, he shook his head. "They don't trust me?" he said, more a question than a statement.

She frowned, quirking her head. "Really? Because Thea adores you. I've babysat a lot of kids and I don't think I've ever seen one with such an attentive older brother."

Oliver was no stranger to compliments. Maybe it came with being the son of a billionaire or maybe it was in part because he was attractive, a fact he was well aware of. But when Felicity said it, he suddenly felt like a stuttering twelve-year-old wearing braces and getting his head pat. "She... I..." He blew out a breath, turning his eyes up, and shook his head. "Speedy's one of my favorite people."

"Speedy," she repeated fondly. "I can see why you call her that. She's fast. Sometimes I can't keep up."

He grinned. "She is. She'll probably turn into a professional runner or something."

"I don't know. I think half the appeal to running is that she always ends up in your arms."

Oliver ducked his head, a flush spreading across his cheeks. He tugged on his hair, covering his face with his hand, wishing his blush would fade, hoping she didn't see.

Felicity didn't tease him, though. She merely smiled at him before she turned back to her books. She had her hair piled up on her head with three or four pencils holding it in place. When it was down, it was all curls, thick and untamed. Sometimes he thought about reaching out and tying one around his finger. Her hair looked soft.  _She_ looked soft.

He was content just to watch her. She got this cute furrow between her brows when she concentrated, and she moved her lips sometimes, mouthing along to the book as she read.

She was the cutest thing he'd ever seen.

* * *

Tommy frequently called him a sap. It was an on-going thing. Felicity had been babysitting Thea for three months and Oliver had cancelled on hanging out with Tommy enough that his best friend knew something was up. Well, no, he figured that out exactly three minutes after Oliver mentioned Felicity for the first time.

"What was that?"

Oliver frowned. "What was what?"

His brow furrowed in confusion. "How you said her name. It was all...  _breathy_."

Oliver's mouth screwed up. "No, it wasn't."

"Yeah, buddy, it was," Tommy laughed. "You sure you don't have a thing for the babysitter?"

Oliver shifted in his seat, turning his eyes away. " _No_..."

"Oh my God, you do!" Tommy clapped his hands. "This is awesome! You're into the hot, older babysitter. Hey, do you think she likes you back? Because that would be  _gold_ …"

Oliver rolled his eyes. "Can we talk about something else? Like how Lisa Terry almost definitely offered to give you a handjob yesterday?"

Tommy smirked. "Lisa Terry almost definitely  _did_ give me a handjob yesterday..."

And so the topic was closed. At least until he casually brought her up again, and then Tommy remembered how amusing and completely clichéd it was that he had a thing for the babysitter.

* * *

Except it wasn't just the babysitter thing. Yeah, sure, she looked cute when she showed up in her tiny skirts and her heart-covered sweaters. She was all blonde hair and pink lipstick and so cheerful when she saw him. She was also smart, though. Like, insanely, almost intimidatingly, smart. Her IQ was way above the usual and she liked taking apart computers for  _fun_. She was at the top of her class and always happy to talk about how she'd be going to MIT the following year. Oliver was always happy to listen, too. It was pathetic, sure (or that's what Tommy said), but he could spend hours just sitting there, listening to her ramble on and on about school and friends and how, one day, she wanted to be working for some big tech company, or maybe even running one of her own.

Felicity was the type of girl that he knew Raisa would tell him he should hold onto. That she was one of those smart, ambitious girls that was going somewhere in her life. That instead of wasting his time on forgettable flings or week-long relationships, he should focus on something  _real_.

Oliver'd had a few girlfriends in his short fifteen years. Nothing serious. He'd spent more time with his hand up the top of girls he  _wasn't_ dating than those he was. A fact that never really bothered him before. Oliver didn't care much for the idea of being tied down. What was the point? There were so many options out there and he wanted to sample them all. But there was something about Felicity that he found captivating. Maybe it was the way she could turn almost anything into a rambling speech that went off in three different directions at once—

_"I'm not saying that one day we'll be overrun by robots, but I am saying that we should probably plan for the worst. I mean, if we're going to play around with artificial intelligence, we should probably have like an emergency death switch, right? Actually, that sounds cruel. Are we responsible for that life, even if it's artificial? Once it becomes sentient, do we consider it an individual and then remove ourselves from the equation or do we still consider it too artificial to be real? Wow, I feel like I just wandered too deep down the philosophy path. You can stop me any time, you know? Just give me a sign to stop and I will. Oh, we should do that! We should come up with like a, 'you've babbled me into a coma' sign so I know when to take a breath."_

—or maybe it was how much she genuinely cared about Thea—

_"Miss Thea, you are the fairest princess in all the land, have I told you lately?"_

_"Only two times today," Thea replied cheerfully, kicking her feet back and forth a she sat atop the kitchen counter._

_"Two times?" Felicity cried in dramatic dismay, putting a hand to her forehead. "What kind of babysitter am I?"_

_Thea giggled, shrugging her shoulders._

_"You know what? To make up for how much I don't show you how awesome you are, why don't we make cookies, okay? Nothing with peanuts, because you don't want to see my Elephant Man impression, but I think we can make something extra chocolaty. How does that sound?"_

_Thea threw her hands up in excitement. "Ollie! Ollie, we're making chocolate chip cookies!"_

_"I heard," he answered, grinning from his place, leaning in the doorway._

_"You, sir, are on mixing duty," Felicity informed him. "You can put those muscles to good use." She paused. "Not that I was noticing your muscles. Because that would be weird. And awkward. Much like everything coming out of my mouth. Which will stop in 3… 2… 1…"_

_Thea laughed. "You're silly."_

_"I'm silly?" Felicity reached for her, taking her by the hands and making her dance side to side. "The silliest silly person you ever met?"_

_"Uh-huh." Thea nodded agreeably._

_"Well, as long as I'm the silliest. I think I can live with that."_

—or maybe it was just that she was, genuinely, the kindest person he'd ever met—

_Oliver was ready to give up. Seriously. This algebra thing was kicking his ass._

_A knock at the door drew his attention, but before he could tell whoever it was to go away, the door swung open and Thea came running inside, screaming,_ "Surprise _!_ "  _so loudly that he heard his hears ring._

_Frowning down at her, he raised an eyebrow to ask why she was surprising him when Felicity's voice intervened._

_"I know you've been studying all day, so Thea and I thought we'd give you a break from it… Consider this your official invitation to 'put away the homework and come eat pizza and rot your teeth with soda.'"_

_"That's nice, thanks, but… if I don't get this done—"_

_"Oliver, you are looking at the queen of studying, all right?" She smiled lightly. "If you push yourself too much, it's just going to make you frustrated and you won't get anything done. So…" She walked toward him, reaching over to close his textbook. "Come on. I'll even let you pick the show. As long as it's age appropriate."_

_He half-grinned, standing from his chair. "All right. Fine. But only for an hour."_

_Saluting him, she turned on her heel to leave._

_Mimicking her, Thea followed her out._

_When he got downstairs and found she'd made his favorite pizza, he realized she'd actually planned ahead to make sure he took a break._

_She really was something else._

* * *

Of course, all good things had to come to an end eventually, and the bubble was ready to pop.

"Oliver?" A knock followed and his head rose quickly, spotting a familiar figure standing by his door.

He stood abruptly, his eyes darting around his room, suddenly worried he'd left something embarrassing lying around. And really wishing he'd taken down that Britney Spears poster of her posing in a bikini top and chaps. Ugh.

"Hey…" She half-smiled, stepping a little further into his room. "So, awkward, but I wanted to talk to you about Thea…"

He frowned, looking past her curiously.

"Oh, she's in bed." She waved a hand behind her. "She zonked out after I read like, three Berenstain Bears stories to her."

He nodded, walking around his desk and toward her, tugging the sleeves of his sweater up his arms. "Sure. So, what's up?" he asked, wondering if he sounded half as cool as he was trying to sound.

"Well, you know how I was telling you about MIT?"

He nodded slowly. "Yeah, you're starting in September, right?"

"Yeah, well, for a graduation present, my mom's paying for me to go on this amazing backpacking trip through Europe. Me and a couple friends are going to spent pretty much the whole summer over there. We've been talking about it for a while but I only saved so much money, so I didn't think I'd be able to go, but then my mom said she was saving up too, and, well, next thing I know, I've got the green light." She was tugging on her fingers awkwardly. "Anyway, I just… I thought I'd have more time to kind of ease Thea into it. She… She's pretty attached to me and I don't want to hurt her. So, I don't know, I guess I was hoping you might have some tips for how I'd break it to her? It's already May and I'm leaving at the end of June, so…"

Oliver stared at her a long moment. "June, uh…  _Wow_ , that… that's soon."

"Yeah, well, I didn't think I'd be leaving for MIT until the end of August, but… I can't pass up on this trip."

"No, yeah, of course not…" He shifted his feet, picking at his thumb with his forefinger. "Uh, yeah, I- I can help you with Thea."

She let out a sigh of relief and smiled at him. "Great. Thank you. I just… She's so sweet and I don't want to hurt her feelings. I mean, babysitting isn't exactly a long-term thing. The kids always grow up. And maybe if I didn't love computers so much, I'd turn it into a real career, but,  _alas_ , the ones and zeroes are my faithful companion."

"You'd be good at it. You'd probably be good at anything."

She flushed, a bright red tint high on her cheeks. "Thanks. Maybe I'll put 'good at child-wrangling' on my resume. Right under 'spends too much time avoiding social situations by taking apart computers and putting them back together,' and above 'occasionally manages to control her embarrassingly broken brain-to-mouth filter.'"

He raised an eyebrow, his head tipped. "Are those skills or warnings?"

She laughed. "Both?"

He grinned, nodding. "So Europe, huh?"

Felicity lasted all of three seconds before she told him every single city, country, and landmark she wanted to visit. And, like usual, he lapped it up like an eager puppy.

* * *

Truthfully, he was disappointed. He'd tried not to think about it, but reality was staring him in the face. After she left, he was probably never going to see her again. He'd never been faced with that issue before. Then again, he'd never really liked a girl this long before. Or this much. And he wasn't even dating her. Hell, the closest he'd gotten to her was wiping flour off her nose when they were baking and shaking her hand when they first met. And the few times he'd put a hand on her shoulder.

That was a thing.

Like when she told Thea that she'd only be there for another two months and then, after that, Thea would have a new babysitter. As expected, Thea cried. In fact, she cried so hard and so long that she eventually fell sleep. And Felicity had been a little broken by it, even second-guessing her trip to Europe in favor of spending another couple of months with Thea.

She was pacing, wringing her hands and chewing her lip. It was a trifecta of worried signals.

"Felicity…"

"I mean, it's just Europe, right? It'll be there in four years!"

"Felicity."

"And Thea's young. It's not good to change things up too frequently. We've built a great bond. I  _really_ like her…"

"Felicity."

"So that's it then, I'll just tell my mother and my friends that I'm not going to Europe. And then, when September comes, I'll find a way to convince Thea that she'll be okay…" She nodded. "Sure, that sounds easy enough." She blew out a sigh and tossed her head back. "Until she get upset that I'm leaving and I have this whole freak out again and somehow convince myself to put MIT off until Thea's old enough that she doesn't need a babysitter. And then where will I be? Huh?"

Oliver put a hand on her shoulder, effectively stopping her from her freak out. He stared her in the eyes as he said, "Hey, you're not calling off your trip to Europe."

Felicity frowned. "It'll be fine, really."

He half-smiled at her knowingly. "You've wanted to do this for a while, remember? Huge opportunity, really excited, pretty much already planned the itinerary…"

"Things can change…"

" _Felicity_." He shook his head. "I know you love Thea.  _Thea_ knows you love her. She'll be upset, yes, but she's four. She'll understand when she's older."

"Really?" she wondered hopefully.

He nodded. "It'll suck at first, but she's tough. She'll get through it."

Shoulders slumping with relief, she nodded. "You're right. Of course you're right. I mean, I'm just one person, passing through her life. Her next babysitter could be amazing." She was smiling now. "And it's Europe!  _Ugh_ , I've always wanted to go. I'd never forgive myself if I passed on it."

As she started getting excited again, he smothered his own disappointment and tried to focus on the fact that he'd done the right thing. Sure, he'd had an opportunity to keep her around for a while longer, but she'd been so excited about Europe. And seeing her start to change her plans, it left his gut feeling hollow. Comforting people that weren't Thea was not his forte and he felt a little awkward trying to make her feel better, but the smile she was giving him, looking up at him like he'd just put the stars back where they were supposed to be, that made any discomfort completely worth it.

* * *

He knew his crush on her was way out of control.

She was older. Graduating high school while he was only just about to go into his junior year. She was a genius while he struggled to get his homework done half the time. She knew exactly what she wanted to do with her life while he couldn't even plan the next day. And she was pretty much the epitome of 'happiness,' friendly and warm to everyone she met, while he was selfish and self-involved and probably too arrogant for his own good. Truthfully, she was out of his league. Not something he'd ever imagined himself thinking about anyone, but the fact was clear enough.

So, when Tommy bugged him and bugged him to take a chance, he didn't. Not because he thought she'd reject him, even though she probably would, but because there was no way that he was anywhere near good enough for her.

* * *

On Oliver's sixteenth birthday, he got embarrassingly, never-live-it-down, forever remember and regret every word,  _drunk_.

He stumbled home just before midnight, aware enough to know his parents would be home by one.

He tripped over the rug as he made his way to the living room, where Felicity was, a book open in her lap.

"Whatcha readin'?" he slurred, flopping down beside her, his head tipped back on the couch.

She raised her head from her book to see him, pausing when she caught sight of just how inebriated he was.

What a fun word. Inebriated. He tried to spell it and failed, falling into a giggling fit.

"Somebody's three sheets to the wind."

He turned his head to see her, letting a wistful sigh. "I'd like to get you between my sheets."

Felicity blinked at him. "Wh-What?"

He smiled at her goofily. " _Felicity_ …"

"Um, yes?"

He shook his head, closing his eyes for a moment. "Jus' like sayin' it."

There was a pause before she said. "Okay… Maybe we should get you to bed," she suggested.

He opened his eyes to grin at her.

"I mean, put you to bed to sleep this off, not… take advantage of you while you're obviously really drunk. Which I wouldn't do, ever." She pushed up from the couch, readjusting her sweater. It had ducks all over it. Little yellow, fluffy ducks. Just like her. She was yellow and fluffy and cute.

"Thank you…?"

Whoops, looked he was saying that out loud. He looked up at her as she walked toward him, a hand out for him to take. "C'mon, drunky, let's get you upstairs before your parents come home and realize you were out celebrating a little more than suggested."

He let her pull him up and leaned heavily against her, an arm around her shoulders, as she towed him toward the stairs.

"Your hair's soft," he said, curling it around his fingers.

"Conditioner does that."

"I always knew it'd be soft…" He leaned into her a little more and breathed her in. "And you smell good. Knew that too."

"I do try to bathe on a regular basis."

He smiled, his head falling back. "You're so… snarky. And smart. Did I say smart? You're really smart. Like, so smart that I probably look dumb to you. Don't I?" He shook his head. "I could be smart. I could study more. Would you like me if I studied?"

Felicity looked up at him, her brow furrowed. "I like you just fine, Oliver." She helped him up the stairs, an arm around his waist. "I'd like you better if you walked faster."

"I can do that." He released her only to run up the stairs, wobbling when he reached the top. "See!" He started imitating Rocky, jumping around and jabbing at the air, but that was a terrible idea…

Felicity caught him as he swayed, nearly toppling down the stairs.

He laughed, leaning on her.

Sighing under her breath, she dragged him down the hall toward his bedroom. "You're  _so_  going to regret this in the morning…"

He stared at her, smiling. "Hey…"

She looked up at him, amused. "What?"

"I'm sixteen," he told her proudly.

"Yes, I'm aware. You made me eat a piece of birthday cake before your friend Tommy dragged you out of the house."

"You should'a come. It was great. We had a party." He leaned in toward her like he was sharing an important secret and whispered, "I got a little drunk." He shook his head. "Don't tell my parents."

Biting her lip, Felicity nodded slowly. "You don't say."

He nodded and then put a finger to her lips to shush her. "You gotta keep my secret though. I'm trusting you."

Felicity smiled.

Oliver's gaze fell to her mouth. "You have really pretty lips."

Clearing her throat, she turned her head away and walked them the last few feet to his door. Pushing it open, she helped him inside and to his bed, pushing him back so he sat on the edge, his hands on his knees.

"Are you gonna be okay from here?" She shrugged. "I'm really just asking to be polite. There's no chance I'm undressing you."

He nodded jerkily, struggling to get his shoes off before eventually leaving one on and falling backwards on the bed, possibly making a snow angel with the blanket.

She disappeared into the bathroom, coming back with Aspirin and a glass of water before she started toward the door, leaving him to his spinning ceiling. But then he called her name, his head turned in her direction and his arm outstretched like he was reaching for her.

"Yes?" she asked, staying by the door.

"D'you think…" He trailed off for a moment, shook his head, and tried again. "If I was older, and smarter, would you like me?"

Frowning, Felicity didn't reply at first.

He groaned, lifting a hand and rubbing it over his face. "Maybe if I just did my homework when it was due…"

Stifling her amusement, she walked toward him, catching his eye. "Oliver, what's this about?"

He huffed a sigh and turned onto his side, his head pillowed on his arm. "You're…  _you_. And I'm…  _me_."

" _Yes_ …" she drawled, still not sure what point he was trying to make.

"But if I was less me and more like you then would you date me?"

Suddenly, her amusement faded completely. "Oliver, do you have a crush on me?"

Groaning, he turned his face down into his mattress. "Who told? Was it Tommy?"

Shaking her head, she crossed the room to stand at the foot of the bed. "Nobody told…" She stared down at him a moment. "You don't have to be less you or more me. I like you just the way you are."

He lifted his head up to look at her. "Really?"

"You're a sweet, charming, funny,  _smart_ guy, Oliver Queen. Anybody would be lucky to date you."

He pouted his lips. "'Cept you… 'cause you're leaving and I'm young and you're pretty and I like it when you ramble and I hope our kids have your brains and smile and…" His own eyes were drifting closed as sleep started to feel like a really good decision.

"Goodnight, Oliver."

"Night, 'Licity…"

She turned off the light when she left.

When he woke up the next morning, he stuffed his head under his pillow and wished he could curl up and die in the corner. It had very, very little to do with his hangover.

* * *

In the weeks that followed his drunken confession, Oliver was stuck between not wanting to be around her because he was embarrassed and not wanting to stay away because he knew she was leaving. But, since she didn't bring it up to rub in his face when he accidentally bumped into her one Friday night, he decided maybe she was going to take pity on him. That didn't stop him from continuously going over what he said, however. She hadn't outright rejected him, but she hadn't really said anything to the effect that she liked him too. It was more like one of those pep talks people gave when they felt bad for the person with self-esteem issues. And, hah, as if he'd ever had self-esteem issues. Only, well, maybe he wasn't as confident or as sure of himself as he thought he was…

* * *

Three weeks passed when she finally brought it up. He came home late from hanging out at Tommy's to find that Raisa had put his dinner in the fridge. He was heating it up when Felicity wandered into the kitchen for something to drink and found him. Instead of leaving after she'd poured herself a glass of water, she took a seat at the island and watched him avoid looking at her.

"We can talk about it, you know, if you want to."

He stared at the floor a long minute. "Is this the part where you tell me I'm a nice guy, but I'm too young for you?"

She smiled at him lightly. "Oliver, you're sixteen year old. You  _are_ young. So am I." She shrugged. "But you're also in high school, and you will be for the next two years, while I'll be halfway through college."

He winced. "When you put it like that, it sounds weird."

"It's not just the age thing, though."

He stared at her. "The smart thing?"

She shook her head. "I don't know where you get the idea that you're not smart. Just because you struggle with algebra doesn't mean you're dumb. You just never apply yourself." She shrugged. "I've seen your test scores. I know you can do better than you do. If you just spent some more time on studying and getting your homework done and in on time, your grades would be a lot better than you think. But, this isn't a lecture on your studying habits. Because, in the end, it's really up to you what you want to do. And changing that for a girl, it's never going to work."

He nodded slowly. "So I'm  _not_ too dumb for you…?"

"Of course not. Intelligence isn't something you can only measure by grades or IQ. You can be smart in other ways. You're smart with people in ways I  _never_  could be. You understand them and how to entertain them and how to keep a whole room riveted on anything you say. That's a talent."

He grinned, shrugging immodestly.

" _But_ …"

His smile dipped.

"I'm leaving for Europe, and then MIT, and even if I wanted to be in a relationship, this just isn't the right time. My mom always said that this is one of those times in your life that should just be about you. About finding out who you are and what you want. And right now, I want to go to Europe and sight-see and spend two months with my two best friends and no other obligations. And in September, I want to go to MIT and embrace college life to the fullest." She shook her head. "It's not that I don't like you, because I do, but the timing isn't right. Maybe if it was a few years from now, I'd be saying something different, but… It's not."

He nodded, half-smiling to show her he understood, even though he could feel his heart caving in a little with every word.

This was pretty much the equivalent of 'it's not you, it's me,' only he never got a chance to actually date her before she dumped him.

* * *

Afterwards, he managed to avoid her for two weeks.

But then school picked up and exams were happening and he actually was spending more time around the house, studying. There was almost no chance he was going to pass algebra with anything but a D, but he was going to try anyway.

As time dwindled away, the inevitable day that she would be leaving approached, looming overhead. His parents had already asked her if she had any friends she wanted to refer, but both of her best friends were going along with her and she didn't trust anybody else enough to leave with Thea. So, they had to put their feelers out elsewhere and hope they came up with someone that Thea would love just as much as Felicity. Speaking of, Thea was getting clingy, demanding more and more of Felicity's attention since she knew that, soon enough, she wouldn't have any of it. Felicity didn't seem to mind, though. On the weekends, she took Thea out to the zoo, even if she did launch into a long ramble about how cruel it was to keep animals in such confined spaces, and out to the park, where she was, as usual, convinced to get Thea ice cream, and to the swimming pool, where she donned floaties since Thea wanted them to match. Sometimes Oliver joined them. He knew it was only making it harder for himself to get over her, but he figured, if he was never going to get a chance, he might as well enjoy her friendship.

And, for all that she'd said she couldn't date him, she was a good friend.

She listened to him complain about school, she helped him make up flash cards for his tests, she covered for him when he went out late to hang out with Tommy even though he wasn't supposed to. He supposed it was just one more thing to add to the list of why she was awesome and he was pathetically in love with her. He never really labeled it, even though Tommy bugged him about it constantly. Oliver had never been in love. He'd loved the attention he got from girls. He loved how much they loved him. He loved knowing that he could get just about any girl he felt like. Except for the one he really wanted.

* * *

Raisa didn't tease him about it.

"Sometimes, we fall in love and the clock, it does not agree. But just because the timing is wrong now, does not mean it is wrong always."

"So what? I'm supposed to wait it out? Four years for her to finish MIT and  _hopefully_ come back to Starling City?" he wondered, frowning down at the heaping bowl of ice cream he'd served himself.

"No, no," she disagreed. "You experience life. You grow up, you go to college, you meet other girls, you fall in love, you fall out of love, and then, maybe, one day, you meet her again. The timing is right, she falls in love with you too, and…" She waved a hand, smiling at him. "Time does not always do what we want  _when_ we want, but sometimes that is a favor it grants us even when we do not know it."

Oliver frowned, digging out a large bite. "Why can't it just be easy?"

"Oh, Mister Oliver," she said affectionately, reaching over to pat his cheek. "If it were always easy, it wouldn't be as special."

Sighing, his shoulders slumped, and he filled his mouth with double fudge ice cream. "Love sucks," he garbled.

"Sometimes, yes," she agreed.

That wasn't the answer he was hoping for.

* * *

On Felicity's last day, he didn't leave his room. It was petty and dumb and he'd probably regret it, but he laid on his bed, convincing himself that watching her leave would be worse. So, he didn't. He stayed upstairs, avoiding her while she was downstairs, spending her last few hours with Thea before his parents got back from some late lunch they were doing with a business associate. School was done, so he had nothing left to study for, nothing to distract him. He simply laid in his bed, staring at the ceiling, trying and failing to forget that, after today, it was over.

Time ticked by, heedless of his misery, until eventually he heard the car pull into the driveway, the one that was returning his parents. He heard the door open and close and waited for the inevitable sound of it repeating to let him know she'd left. A part of him wanted to get up and move to the window, to watch her little red bug pull away down the driveway and take off into the distance. But he didn't. He stayed resolve, lying in his bed, his hands balled up into fists.

He counted in his head, like he sometimes heard her do when she was nervous and wanted to find her control. He counted to ten and then twenty and thirty and forty.

He was on 67 when his bedroom door opened.

He lifted his head, wondering if it was Thea. If she'd barrel inside and crawl on his bed, curling up against him and telling him all about how Felicity was gone now and how she already missed her.

But the sight that greeted him wasn't Thea; it was Felicity.

She stood, uncertain in the doorway, for a handful of seconds. Fidgeting, she tugged on the end of her dress, a pretty white number with a pink pattern. Biting her lip, she reached back and closed his door before she crossed his bedroom, tucking her long hair behind her ears. She didn't say anything, nor did she pause, before she climbed up onto his bed and straddled him, sitting herself on his lap. She pressed her hands down on the mattress on either side of his shoulders. Staring at him a long moment, she seemed to come to a decision. Leaning down, she stopped herself just a few short inches from his mouth. She found his eyes, searching his gaze for a long moment, and then erased that distance between them. Her mouth parted, only to close gently around his bottom lip. A shaky breath left him as she kissed him, and it  _was_  her kissing him, while he waited, watching, wondering briefly if this was a dream he'd cooked up.

She kept her eyes on him, open, kind, as she slanted her lips over his once, twice, and then suckled his top lip between hers, tugging on it lightly with her teeth. He reacted then, his hand reaching up, sliding into her hair and curving around her neck. He tipped his chin up and met her mouth, letting his tongue trace over her bottom lip. Their noses brushed lightly as she leaned down, her chest meeting his. He felt her fingers creep up over his shoulder, tightening around the fabric of his shirt.

Her lips were soft, just like he'd always known they'd be. Her lipstick was bright and he wondered if,  _hoped,_  it might stain his mouth, leaving behind traces of her long after she was gone. He reached up to stroke her hair back, tendrils of it whispered over his cheeks and fell against his neck, pooling in the hollows and tickling at his skin. He dragged the pads of his fingers over her cheek, memorizing it as he pressed long, sipping kisses to her mouth, promising himself he'd never forget the exact shape of it.

She was panting, her harsh breath meeting his own, and their kisses were speeding up, the intensity becoming hard to ignore. It'd be so easy. So  _right_ to turn them over. To slid her dress up her hips and curl his fingers under the sides of her underwear. To part her legs, wrap them around his waist, and sink himself inside her. To hear those little gasps he could just imagine her making, her breath hitching against his ear as he moved inside her. And his name, tumbling from her mouth, as he made her come.

But then he heard Thea in the distance, shouting Felicity's name, demanding that she come out from wherever she was. He had no doubt that Felicity made some excuse, giving herself only a few minutes to say goodbye to him. He wasn't sure if she'd planned to kiss him, or for it to get this far, but it had.

He cupped her jaw, staring up at her, their lips a breath apart.

For a first kiss that  _should_ have been a beginning, it tasted a lot like an end.

"Is this how you say goodbye to everyone?" he murmured, reaching up to stroke her hair back, tucking it behind her ear.

She shook her head. "No, only the cute older brothers of the girls I babysit."

He raised an eyebrow. "Are there a lot of us?"

She laughed, a soft, intimate sound that made his heart thud. "Just you."

He hummed, his thumb falling to rub over the arch of her cheek. "You have to leave."

"I do."

He ground his teeth together and shook his head. "Probably never gonna see you again."

She stared at him, not agreeing or disagreeing. Instead, she pressed one last, firm kiss to his lips and then she climbed off of him and off the bed and she walked to his door, smoothing out her dress as she went. She looked back as she reached for the door handle, and he propped himself up on his elbows to watch her go.

With a soft, sad smile, she left, closing the door behind her.

The first time he met her, he thought it was love.

He didn't know for sure until she was gone.

* * *

He was twenty-six before he saw her again.

Like Raisa had told him to, he'd lived his life. Gone to college (four, to be exact), dated other girls (Laurel, Sara, Shado, McKenna, and Helena being a few of the memorable ones), made mistakes (see his previous girlfriends and his relationship history in general), straightened up (apparently he made a good firefighter), and finally figured out how he wanted his life to be (happy; whatever that meant).

His mother was hosting a fundraiser for fire house 52. He'd dressed up, digging out one of the few suits he kept around for occasions just like this. He wasn't the same guy he'd been a few years ago and now found the tie even more suffocating than usual. Across the room, sipping champagne by the buffet, he could see his captain, John Diggle, snickering at his discomfort. Sure, Diggle knew that he was the reason their house was going to be getting a generous donation today, but that didn't change anything. Oliver was one of the guys, whether he came from money or not. And that, despite how irritated he was, actually made it worth it.

The fundraiser had been in full swing for more than an hour. That was exactly fifty minutes longer than he wanted to be there. But he had a duty to play the good son, talking up anybody he met about how vital and meaningful the fire house was and how their donations were going to a good cause. Sure, to him it seemed obvious. Firefighters were necessary. Who wouldn't want to donate to that? But apparently people liked to be schmoozed and, even if he was a little rusty, he was still good at it.

"Oliver!" he heard his mother call.

He turned to see her, elegant in an expensive dress and wearing jewelry from the family vault. She waved at him to join her where she stood cradling another woman's hand with familiar affection. He couldn't see who from this angle, but she was slim, with blonde hair falling down her back, and a pink dress that said she was acquainted with designer labels and their cost.

Beaming at him, Moira said, "We've just had our largest donation yet," she informed him as he approached. "You might not remember her, it's been nearly ten years…"

His brow furrowed as he came to a stop beside his mother, only to lay eyes on Felicity Smoak. She was older, of course, but no less pretty. In fact, he thought she was even more beautiful than he remembered. She reached up to tuck a curl behind her ear and he found his eyes automatically straying to her fingers, searching and, thankfully, not finding a ring, engagement or otherwise.

"Oliver, this is Felicity Smoak, she used to babysit for your sister…" Moira cast her eyes around, searching for her daughter before focusing back on the woman across from her and smiling warmly. "Miss Smoak is CEO of her own company. Smoak Screen Tech. She's been doing an  _amazing_  job. Walter won't stop reminding me that he nearly convinced her to sign on with Queen Consolidated before she decided to go her own way and build up a company of her own."

"It was a tempting offer and Mr. Steel is a great businessman, but I had to go with my heart."

"Well, it looks like your heart was the right choice if you're doing well enough to have both my mother and Walter this excited," Oliver noted.

Felicity smiled up at him. "Your mother is being generous. We're not quite as large scale as Queen Consolidated, but we do well. And everything is my design so far, so I can't say I'm not proud."

"Oh, I think I see Thea…" Moira held up a finger. "I'll be right back. She talked about you for years, comparing every babysitter she had to you."

Felicity flushed at the praise, ducking her head.

Moira hurried off to find her daughter, leaving the two of them alone.

"So…" Felicity looked up at him. "A firefighter, huh?"

He shrugged. "Apparently my talents laid more in saving people than it did running a business."

"I can see that."

He tipped his head. "Yeah?"

"Sure. You were always a hero in Thea's eyes."

He laughed under his breath. "Yeah, well, she was easy to please as a kid."

Felicity rolled her eyes. "Oliver, you used to spend hours doing everything to make her laugh. Don't forget, I was there, I saw all the goofy faces and dancing."

He rubbed the back of his neck. "Some of that was probably just to get your attention," he admitted.

She bit her lip. "You got it."

He stared at her, his heart thudding a little faster in his chest. "You know I liked you as soon as I met you… I think I started crushing on you as soon as I opened the door."

She laughed, a blush filling her cheeks. "Well, I do remember wearing a particularly short skirt at the time."

He chuckled, shaking his head. "That helped…. But there were other reasons." He licked his lips. "How you were with Thea; that was a big one. And how you talked to me, treating me like a person instead of a trust fund or… the image I'd kind of built up. That was different for me."

She smiled. "It was one of my favorite babysitting jobs… And it wasn't just because I loved hanging out with Thea."

He raised an eyebrow down at her.

"Oliver, I wasn't just trying to make you feel better. You were charming and sweet and I liked you  _long_  before you drunkenly confessed your feelings..."

He winced, turning his eyes up. "Not one of my finer moments…"

"No, but definitely a memorable one."

"I hold my liquor better now," he told her. "I haven't drunkenly confessed my love for someone in… weeks."

She laughed, her shoulders shaking a little as she pressed her fingers to her mouth. Looking up at him through her lashes, she asked, "So how did you end up becoming a firefighter, anyway?"

He inhaled deeply and shrugged. "I… I was kind of lost for a while. Girlfriend broke up with me, again, and I got tired of being in that same rut… Saw something about looking for volunteer firefighters and, next thing I know, I'm serious about it. And I like it, I really do. It's… amazing. Doing something like that, saving lives. I mean, I was always kind of an adrenaline junkie, bored too easy and always looking for a thrill. So it's probably the best job for me."

"Well, I don't think anybody can say it's not something to be proud of," she mused.

"I don't know. I think if my dad were still alive, he might have something to say… He always had expectations that I'd take over QC when he retired."

Felicity reached for him, a hand falling to and squeezing his forearm. "I heard he died. He was always very kind. I'm sorry you lost him."

Oliver nodded, still feeling a twinge in his heart that was all too raw. "I miss him. A lot, actually. We didn't always see eye to eye, but…"

"He was your father," she said softly, knowingly.

He stared at her a moment. "Yeah." He blew out a breath. "Lost chances, I guess. You never really know what you have until it's gone."

Felicity's nose wrinkled. "I've never liked that saying."

"No?"

She shook her head. "It's depressing. It's supposed to remind us not to take anything for granted, but usually it's too late."

His brows hiked. "Sometimes you learn you lesson, sometimes you don't."

She paused for a moment before wondering, "Have you?"

"About wasting time and chances…" He nodded slowly. "But then, I took my chance when I was sixteen. My timing just sucked."

Felicity smiled, her gaze dropping for a minute, eyelashes dusting against her cheeks. When she looked back up at him, she raised a challenging eyebrow. "How's your timing now?"

Oliver let out a small laugh under his breath. "You tell me."

She cast her eyes away for a moment. "Your mother and sister are going to be on us in 5… 4… 3…"

He kissed her.

Burying a hand behind her neck, he tipped her head back and slanted his lips across hers. It was just as new and as familiar as he expected. He felt her hands on his chest, gripping the front of his jacket, and he had a flash to her fingers wrapped around the thick suspenders of his firefighting suit. He slid an arm around her waist and pulled her in close, kissing her a little more firmly, smiling as she hummed happily against his lips.

This time around, his timing was perfect.

* * *

It'd taken a lot longer than he expected, they had a lot of catching up still to do, but Raisa had it right when she said that time had a way of making things happen when it was right.

A year after the fundraiser, Oliver proposed to her, standing on a ladder at their apartment window, his team standing below, cheering him on from where they stood on the fire truck. Felicity grabbed him by his suspenders, pulled him in for a kiss, and said yes.

They were married on the anniversary of their first kiss.

As it turned out, not only was Felicity his first love, she was also his last love.

{ **end**.}

**Author's Note:**

> so apparently au's are like, my favorite thing to write ever! seriously, this was so much fun. slightly-older!felicity with lovesick!oliver is literally the best to write. she's all confident and comfortable and he's all 'pretty girl is pretty.' haha. but seriously, this was fun. I love writing an oliver who is just super taken with felicity and schmoopy about her. also the drunk scene was so amusing to write.
> 
> Oh, also I stretched the 'first kiss' thing, because, yeah right Oliver didn't get his first kiss until 16. It was more like his first kiss where he actually cared/loved the person he was kissing. :)
> 
> I hope you enjoyed this. it was supposed to be short (I feel like I say that a lot) but this is what happened instead.
> 
> thank you for reading! please leave a review; they're my lifeblood!
> 
> - **Lee | Fina**


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